The issue of fictional failure which appears like a roadblock is interesting, and tricky to handle, I think. I haven't seen an RPG do it particularly well (except for games which allow you to edit the story more like an author, like PTA or some storytelling games I've played - the more "author/storyteller stance" there is going on, the easier it is to enable).

However, Vincent, your example of the boat-builders is something I can address!

I think that, in a story like that, you're either dealing with a problem-solving and resource-managing challenge (i.e. the characters decided not to put the rope on the ship because they ran out of time to figure out how or why to do it) or a meaningful story beat which is being foreshadowed in advance and carries meaning. The latter is most like a moral tale.

This is interesting, in practice: we are building anticipation and logical foreshadowing by describing how the characters attempt to build the boat, the choices they make, their oversights or seemingly clever decisions, and then that pays off in the long run (dramatically speaking).

I think that, in such a situation, the only way to make it happen is to *get all the players to buy into it* together. We have to be committed to building up those bit of foreshadowing and looking forward to finding out how it all turns out. The game must be focused on that, in other words, and give some guarantee (even an uncertain guarantee!) that it will pay off.

I think it would be a pretty interesting to say that, hey, this thing is important:

* We're working hard on building this boat.
* Because our characters are like THAT - or because they have these flaws or these character strengths - they make THIS meaningful decision.

Later, in an important moment in the story/game, we know that it will matter. I think it would be most interesting if we didn't know HOW it will matter.

The most obvious mechanic:

We arrive at a turning point (the storm, in this case), and we roll to see what impact the decision to leave out that rope has.

On a poor roll, it is our downfall: our characters were overly proud and they overlooked an important point - because of this, the ship snaps in half and they drown.

On a good roll, it is the opposite: the rope would have limited the ship's flexibility and it's only without it that they were able to survive the storm. (Heck, perhaps we then find out that every other expedition - with that rope in place - never made it, and they are the first to make the crossing!)

Either way, though, that decision should be meaningful, so we can all contribute to it and make it significant, building on it from the very start (as a good author does), creating a sense of inevitability.